(2R,3S,4S)-4-Benzyloxy-2-methyl-pentane-1,3-diol | 1026597-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4S)-4-Benzyloxy-2-methyl-pentane-1,3-diol
• 英文别名: (2R,3S,4S)-2-methyl-4-phenylmethoxypentane-1,3-diol
• CAS: 1026597-32-9
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: IXQMSXDHVMWQGK-MDZLAQPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-4-Benzyloxy-2-methyl-pentane-1,3-diol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 生成 (2R,3S,4S)-2-methyl-4-(benzyloxy)-1,3-(isopropylidenedioxy)pentane
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036
• 作为产物：
  描述：

  (S)-2-苄氧基丙醛 在 Lindlar's catalyst 、 magnesium bromide sodium tetrahydroborate 、 二甲基硫 、 氢气 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 3.42h， 生成 (2R,3S,4S)-4-Benzyloxy-2-methyl-pentane-1,3-diol
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036

文献信息

• Ester derived titanium enolate aldol reaction: chelation controlled diastereoselective synthesis of syn -aldols
  作者：Arun K Ghosh、Jae-Hun Kim

  DOI：10.1016/s0040-4039(00)02227-9

  日期：2001.2

  A chelation controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of commercially available l-phenylalaninol derived esters with a variety of bidentate oxyaldehydes proceeded with excellent syn-diastereoselectivities and isolated yields.

  描述了螯合受控且高度非对映选择性的合成顺式醇缩醛。可商购的1-苯丙的醛醇缩合反应衍生的酯与多种具有优良的二齿进行的oxyaldehydes顺-diastereoselectivities和分离收率。
• Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes
  作者：Arun K Ghosh、Jae-Hun Kim

  DOI：10.1016/s0040-4039(02)01113-9

  日期：2002.8

  A chelation-controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of (S)-valinolderived ester with a variety of aldehydes proceeded with high syn-diastercoselectivities (up to 99:1) and isolated yields (94%). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes
  作者：James A. Marshall、Xiao Jun Wang

  DOI：10.1021/jo00030a036

  日期：1992.2

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.